Ask the Gentleman 2022

Etiquette & Style for the Modern Gent

Being a modern gentleman isn’t just about dressing well and knowing which fork to use at a dinner party, so we asked The Gentleman to chime in and answer your most pressing etiquette questions. Here’s his expert advice on everything from regifting to splitting the check.

Are there guidelines on when you are – or aren’t – supposed to tuck in your shirt?

To tuck or not to tuck; that is the question. As a general rule, you can look to the shirt’s design to identify if it’s meant to be tucked in or not. Straight hems should be left untucked, while curved hems – which you’ll often see in business shirts – should be tucked in. It’s also important to consider the occasion and the dress code. The more formal the event, the greater the likelihood that you’ll need to tuck in your shirt. A few examples: Polos and t-shirts worn to casual occasions should be untucked. Black-tie events and formal business meetings will almost definitely require a tucked shirt. For a business casual look, tucking your shirt is never a bad idea, especially if you’re also sporting a blazer or sweater. Just remember that no matter the occasion, if you’re tucking in your shirt, always wear a belt – this will tidy up your outfit while also ensuring your shirt stays tucked in. On the other hand, if you’re wearing your shirt untucked, the belt is optional.

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On Christmas and birthdays, I
sometimes receive things I either have too much of (like coffee mugs) or will never use (like cologne). Is it rude to regift these items to someone who might actually use them?

Believe it or not, regifting unwanted presents can be done in a tactful way – if you follow a few simple rules. When regifting, always make sure you regift outside of that social circle; for example, if your co-worker gives you a coffee mug during Secret Santa, don’t turn around and give it to another colleague. You never want the original gift-giver to find out you’ve regifted their gift. Instead, you might pass the mug along to your brother-in-law. Another consideration is used vs. brand-new items. Anything brand-new is fair game, but items that have been opened or used should either be sold, kept, or donated. If the gift is handmade, or if it has special significance to the gift-giver, don’t give it away; when someone takes the extra time to make you something, it’s considered bad form to regift it. Similarly, if you are gifted homemade food (say, freshly baked brownies) that you aren’t planning to eat, simply share the treats rather than framing them as a gift for another person. Finally, be thoughtful when you’re regifting. Instead of getting rid of the unwanted item at your first opportunity, consider who in your life might truly appreciate the gift – after all, it’s the thought that counts.

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My girlfriend and I have been dating for five years, and her mother keeps asking us when we’re getting married. She’s even started to bring up the subject publically at family gatherings. While my girlfriend and I want to get married someday, it’s just not something we’re in a rush to do. How can we politely ask her to stop pressuring us?   

Parents want to see their child get married for all kinds of reasons: They want a wedding to plan, they want grandkids, or they simply want to see their child settled and happy. If you know what your girlfriend’s mother is motivated by, try to throw her a bone. You might tease her about grandchildren or reassure her that a wedding is on the horizon … someday. If her mother is truly being insufferable – especially in public settings – you may ask your girlfriend to pull her aside and gently point out her faux pas. “Mom, I know you want us to get married, but calling us out publically is not helping to speed things along.” Just remember that your girlfriend’s mother most likely has her best interests at heart, and a little bit of patience – both hers and your own – can go a long way in cementing your relationship.

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When going out to eat with my friends, I always have one buddy who suggests we split the check evenly, and everyone else quickly agrees. But most of the time, my order costs a lot less than everyone else’s because I don’t drink. How can I ask to pay for my order only without upsetting my friends?


Splitting the check is hardly ever fair, especially when your friend orders steak and wine to your salad and water. In these situations, it’s best to politely request separate checks at the beginning of the meal – not only will it make things less awkward among your friends, but it’s also easier on your server. You could use this moment to explain to your buddies that you’re on a tight budget, or that you simply don’t plan to order drinks like everyone else. A good friend will understand and may even appreciate you breaking the cycle of the split check. If the thought of speaking up makes you uncomfortable, you might consider asking one of your other friends to advocate for you; they could say, “Hey, Jason only ordered a sandwich, so let him pay his share and we can split the rest.” Another tactic to try is ordering last – that way, if a split check is inevitable, you can at least order as much as your friends and make it a good meal.

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I have a Zoom job interview coming up and want to put my best foot forward (virtually, that is). How can I impress my interviewer using this online format?

Interviews are already a nerve-wracking experience, and that’s without the potential for technical hiccups hanging over your head. Fortunately, there are a few things you can do to ensure the Zoom interview is as seamless as possible. First, prepare as you would for any interview – study the job description, practice interviewing with a friend or mentor, and plan out your professional attire (yes, you actually need to wear pants). Second, prepare the space where you’ll be conducting your end of the interview. You’ll want a clean, quiet, brightly lit room with good internet connection and zero distractions. Last, make sure you’re on time (or early!) for the interview. Look straight into the camera when you’re speaking, maintain good posture, and don’t forget to smile.


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